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Aakash GuptaAakash Gupta

What this $2.45B CPO knows that you Don’t!

Jeremy Epling has led product at every level - Microsoft, GitHub, and now as Chief Product Officer at Vanta. In this episode, he unpacks what most PMs get wrong about strategy, what he learned from Satya Nadella, and how AI is reshaping product development. We cover: Preview – 00:00:00 Working at Internet Explorer – 00:02:05 Why He Encourages AI Prototyping Tools – 00:06:15 Ad (Linear) – 00:09:56 Ad (Amplitude) – 00:10:48 AI Prototyping Tools Impact Continued... – 00:11:23 How a Microsoft Feature Gets Built – 00:15:47 Changes in PM Role Inside Microsoft – 00:17:57 Lessons Learned From Satya – 00:20:59 Steps to Move Up the Career Ladder – 00:25:11 Ad (Maven) – 00:30:45 Communication as a Step in the Career Ladder – 00:31:33 Moving Beyond the Product – "The Final Step" – 00:34:11 GitHub for PMs – 00:37:33 Experience as a VP – 00:42:33 Evolving Expectations of Director-Level Roles – 00:48:51 Getting Job in Vanta – 00:51:59 Secret Behind Vanta's Success – 00:58:01 Growth in PLG vs. Enterprise – 01:01:36 Unique Things About Building a Product – 01:03:57 Embracing All AI Software – 01:07:16 Evaluation of PMs at Vanta – 01:11:12 Advice to PMs With No Experience – 01:13:56 Podcast transcript: https://www.news.aakashg.com/p/jeremy-epling-podcast 💼 Check out our sponsors: Linear: Plan and build products like the best - https://linear.app/partners/aakash Amplitude: Try their 2-min assessment of your company’s digital maturity - https://bit.ly/4hl25RG Maven: I’ve launched my own curation of their courses - http://maven.com/x/aakash 👀 Where to Find Jeremy LinkedIn: https://www.linkedin.com/in/jeremy-epling-j40 Vanta (Get $1,000 off with our link): https://www.vanta.com/lp/demo-1k?utm_campaign=1k_offer&utm_source=product-growth&utm_medium=podcast 👨‍💻 Where to find Aakash: Twitter: https://www.twitter.com/aakashg0 LinkedIn: https://www.linkedin.com/in/aagupta/ Instagram: https://www.instagram.com/aakashg0/ 🔑 Key Takeaways 1. Big companies teach you how to scale. Great ones teach you how to focus. At Microsoft, Jeremy learned how to operate at massive scale - teams, systems, legacy complexity. But it wasn’t until GitHub that he saw what it meant to focus on developers, ruthlessly prioritize, and ship with empathy. 2. “Strategy” isn’t about having a roadmap, it’s about knowing what not to build.He learned early on that the best PMs aren’t the ones who ship the most features. They’re the ones who create clarity, say no often, and focus the team on why they’re building something, not just what. 3. Prototyping is the new PM’s superpower. At Vanta, every PM gets access to V0. Why? Because the fastest way to learn is to build. His philosophy: “If I can show it, I can test it. If I can test it, I can learn.” 4. The lines between PM, design, and engineering are gone. At high-functioning companies, designers submit pull requests, engineers make design calls, and PMs prototype. Roles are fluid, and the best teams adapt to each other instead of clinging to old job descriptions. 5. Most PMs don’t understand GitHub but they should. You don’t have to be technical to learn GitHub. You just have to be curious. The best PMs at GitHub - even the non-coders - understood the dev workflow, knew what a PR felt like, and respected the architecture. That empathy changed how they built product. 6. Want to grow into VP-level roles? Improve your business acumen. Shipping features won’t get you there. Understanding margin, pricing, GTM, and how your product makes money will. He didn’t start out as a “business” PM, but he made a point to learn the mechanics of how things grow and that’s what unlocked leadership roles. 7. If you’re doing the same job after 4 years, you’re probably not growing. He kept switching teams every few years at Microsoft not because he was bored, but because growth requires friction. Every new domain forced him to relearn how to build, lead, and communicate. 8. Satya Nadella didn’t just save Microsoft, he redefined what it meant to build product there. Under Ballmer, the strategy was “build everything.” Under Satya, it became “build what matters.” He saw firsthand how Satya’s obsession with clarity and developer-first thinking rewired the org. That’s what made it the best place for PMs to work back days. 9. Letting go is the lost art for PMs! One of the fastest ways to grow as a PM? Kill projects that don’t matter even if they were your idea. According to him, the PMs who get promoted are the ones who know when to let go and when to keep building on the idea. #strategy #microsoft #ai 🧠 About Product Growth: The world's largest podcast focused solely on product + growth, with over 170K listeners. Hosted by Aakash Gupta, who spent 16 years in PM, rising to VP of product, this 2x/ week show covers product and growth topics in depth. 🔔 Subscribe and like the video to support our content! And turn on the bell for notifications.

Jeremy EplingguestAakash Guptahost
May 25, 20251h 19mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Vanta CPO on product leadership, AI tools, and career growth

  1. Product management evolved from waterfall PRDs and inward decision-making to broader PM scope, stronger design partnership, and tighter customer-and-business accountability.
  2. AI prototyping and coding tools (e.g., v0, Lovable, Bolt, Cursor) are changing how product, design, and engineering overlap, enabling faster prototyping and shorter feedback loops.
  3. Career progression in product often hinges on creating focus (learning to say no), making hard cuts (even in your own area), rotating to learn new domains, and expanding into end-to-end business ownership.
  4. At exec levels, impact comes from staying close to the product while owning pricing/packaging, go-to-market alignment, customer roadmap communication, and always-on operational accountability.
  5. Vanta’s growth is driven by automating painful compliance workflows for startups while expanding into broader “trust management” pillars for enterprises, with an emphasis on UX craft and platform foundations.

IDEAS WORTH REMEMBERING

5 ideas

Focus is a career accelerant: learn to say no early.

Epling’s first promotion came from demonstrating prioritization discipline; leadership rewards PMs who reduce noise, clarify what matters, and protect teams from low-value work.

Cutting your own roadmap can signal strategic maturity.

He earned advancement by recommending large scope reductions and reorienting effort to higher-leverage work, showing he could evaluate impact beyond local team momentum.

AI tools make “seeing is believing” practical at speed.

Giving every PM access to tools like v0 enabled rapid interactive prototypes that can be shown to customers for immediate feedback, reducing dependence on long documents as the primary artifact.

Role boundaries will blur, but accountability should stay clear.

Epling welcomes overlap (PMs prototyping, designers contributing closer to implementation) while maintaining design accountability for the shipped experience—not just the Figma deliverable.

Exec impact scales through business ownership, not feature output.

VP/CPO work expands into pricing/packaging, sales enablement, solution engineering alignment, customer roadmap calls, and narrative clarity for CEOs—without losing product closeness.

WORDS WORTH SAVING

5 quotes

I remember the first promotion I got at Microsoft, and I remember one of the things my manager said with me that obviously I've never forgotten was like, "You're getting this promotion because you've, like, learned how to say no."

Jeremy Epling

This process is extremely hard and, you know, takes months and months and, like, a year or more. It costs $100,000 or more, and we're like, "Hey, how can we bring software automation to this?"

Jeremy Epling

If you're comfortable, that should be some level of a warning sign to you that, like, you have now learned everything you need to go learn.

Jeremy Epling

They build these great HR systems that are, like, you know, like MMO RPGs, where there's, like, twice the amount of levels and you're slowly moving up and you're always just about to get the next promotion.

Jeremy Epling

I think that's when things get bad, when it feels like you're just a translation layer, you know?

Jeremy Epling

Microsoft PM in early 2000s: specs, waterfall, detachment from customersPM-to-engineer ratio and expanding PM scopeAI prototyping and direct-manipulation UX vs chat-onlyDesign accountability: from Figma handoff to shipped craftSatya Nadella leadership: clarity, priorities, developer focus, acquisitionsCareer ladder: saying no, cutting scope, rotating teams, communicationVanta strategy: compliance automation to trust management platform; PLG vs direct sales

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